详细记录  
题名:Transnitrosation of thiols from aliphatic N-nitrosamines: S-nitrosation and indirect generation of nitric oxide.
作者:Yanagimoto T, Toyota T, Matsuki N, Makino Y, Uchiyama S, Ohwada T.
来源:J Am Chem Soc[IF=7.419]. 2007 Jan 31;129(4):736-7. No abstract available.
URL :http://dx.doi.org/10.1021/ja0658259
日期:070415
摘要: Takahiro Yanagimoto, Takeshi Toyota, Norio Matsuki, Yumi Makino, Seiichi Uchiyama, and Tomohiko Ohwada*

Laboratory of Organic and Medicinal Chemistry and Laboratory of Chemical Pharmacology, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

ohwada@mol.f.u-tokyo.ac.jp

Received August 10, 2006

Abstract:

S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of S-transnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO. 8:

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